Black Mass

It was a fatal attraction to the seductive personality of Whitey Bulger. Bulger was magnetic in the reverse glamour way of elite gangsters who break all the rules and revel in it. For Connolly, it was an enthralling prospect, a future assured. Working with Whitey. What could be better? What could be easier? It sure beat being one of 250 selfless agents riding around in a government car. Whitey would be the head on Connolly’s glass of beer.

In the first few years of his renewed relationship with Whitey Bulger, Connolly’s “209” informant reports were split between accounts of disenchantment within the ranks of Gennaro Angiulo’s chronically unhappy Mafia family and more concrete tips about Bulger’s rivals within South Boston. Connolly did not remind Bulger that he had originally pledged to inform only about the Italians. And while the Mafia information was mostly generic gossip about problems in the House of Angiulo, the rat file on South Boston came with addresses, license plates, and phone numbers. For instance, Tommy Nee, one of a handful of homicidal maniacs who were regularly committing mayhem out of South Boston barrooms in the 1970s, was arrested for murder by Boston police, with an assist from the FBI, in New Hampshire—just where Whitey said he would be.

But the FBI priority was the Mafia, not sociopaths like Tommy Nee. Through Flemmi, Bulger found out that Angiulo had removed his office phone for fear of wiretaps. Angiulo and his brothers, Bulger told Connolly, were talking only on walkie-talkies. Gennaro was “Silver Fox” and Donato Angiulo was “Smiling Fox.” Bulger even recommended a Bearcat 210 automatic scanner to monitor conversations.

In the button-down FBI office in Boston, such reports were impressing the top bosses, even as Connolly’s increasingly brash ways were irritating his colleagues, who began to jokingly call him “Canolli” because he dressed and acted like a slick mob dude. Jewelry. Chains. Pointed shoes. Black suits. But for his part, Connolly was unconcerned. He knew what he had in Bulger and what it was worth to his career. Bulger’s 209 files were a coup for him and a coup for the bureau, a synergy possible only because of who he was and where he came from. South Boston Irish. “Whitey only talked to me,” Connolly bragged, “because he knew me from when I was a kid. He knew I’d never hurt him. He knew I’d never help him, but he knew I’d never hurt him.”

But sometimes in Whitey’s world, not hurting could be very helpful.

CHAPTER THREE

Hard Ball
As District Attorney William Delahunt was getting into his car to drive to a restaurant near his Dedham office, Whitey Bulger and two associates were barreling down the Southeast Expressway toward the same destination just outside Boston’s city limits. Delahunt was meeting another prosecutor for dinner. The mobsters were planning to terrorize the restaurant’s owner, who had stiffed them on a $175,000 debt. In one of life’s strange split screens, each party would do its business on a different side of the same big room in the Back Side Restaurant.

It was 1976, and the thirty-five-year-old Delahunt had been Norfolk County district attorney for only a year—just a little longer than Whitey Bulger had been teamed up with John Connolly and the Boston office of the FBI. But the chance encounter was not the only thing the DA and the gangsters had in common. One of the mobsters in Bulger’s crew, Johnny Martorano, had been a grammar school classmate and schoolyard rival of Delahunt’s. They had even been altar boys together.

When Delahunt looked up from a table near the bar, he recognized the Winter Hill hitman immediately. Martorano ambled over and sat down, while the other two gangsters hung back. The former school chums shared a drink and got to jiving each other about their opposite lots in life. Johnny Martorano jabbed Billy Delahunt about there being more honor in his world than in the one populated by bankers and lawyers. Delahunt just chortled and did not argue the point with him. But when it was Delahunt’s turn to dish it out, he touched a nerve. Delahunt urged his old classmate turned gangster to stay out of Norfolk County. Stick to Boston, “for both our sakes,” Delahunt cautioned.

Martorano told Delahunt to pound sand, and the repartee got animated enough that one of Martorano’s companions joined them at the table to see what was going on. Bulger hung back, waiting by the entrance and out of sight, but Delahunt certainly recognized Martorano’s companion, Stevie Flemmi. Then the odd encounter ended suddenly, and amicably enough, when Delahunt’s dinner companion, federal prosecutor Martin Boudreau, arrived at the table. When they were alone, Delahunt rolled his eyes and said, “You’ll never guess who I was talking to.”

Meanwhile, Bulger joined Martorano and Flemmi, and the threesome picked a cocktail table against the back wall and set up there. Arms folded, they sat waiting for the owner to appear. They had come to see Francis Green because Francis Green had some explaining to do.

About a year earlier Green had borrowed $175,000 from a high-interest Boston finance company for a real estate investment. The problem was that Green had not paid back a dime and, while he didn’t know it, was stiffing a friend of Winter Hill’s. Whitey knew a way to solve such bad debts. It was not genteel.

Green came into the large central room, spotted the three gangsters, and slid into an empty seat. As was his wont, Bulger skipped the small talk. “Where’s our money?” he asked. Green, a glib salesman with a checkered past, tried a salesman’s tap dance. His finances were in shambles. His business deals had gone bad. He was in bad shape. This had to count for something.

But Bulger would have none of it. No money is no answer. It didn’t matter that two prosecutors were seated across the way. Bulger leaned into Green’s face, his eyes cold marbles. Understand this, Bulger told him, “if you don’t pay, I will absolutely kill you. I will cut off your ears and stuff them in your mouth. I will gouge your eyes out.”

Then Bulger leaned back. He told Green he really should make an appointment with his loan officer to arrange a schedule for repayment. And Flemmi, playing the good cop to Bulger’s tough cop, advised Green to pay something real soon. That way, comforted Flemmi, no one would get hurt. Then it went back to Bulger, who made one final chilly comment: make it $25,000 within a few days.

An ashen Green said he would see what he could do. The brisk business meeting was over. An FBI report afterward recorded in leaden government prose that the conversation “greatly upset” Green. It was an understatement. Green was in fear for his life, and it was fear mixed with bewilderment. He was aware that Martorano and Delahunt had earlier been mingling at the bar, and the entire scene that night left him confused about what exactly he was up against.